Thionyl Chloride-Benzotriazole in Methylene Chloride: A Convenient Solution for Conversion of Alcohols and Carboxylic Acids Expeditiously into Alkyl Chlorides and Acid Chlorides by Simple Titration

Abstract

A solution of 1:1 equivalent of thionyl chloride and benzotriazole in dry methylene chloride efficiently transforms alcohols and carboxylic acids into the corresponding alkyl chlorides and acid chlorides respectively at room temperature, with excellent yields by simple titration.

A palladium catalyzed atom-efficient cross-coupling reactivity of triarylbismuths with α,β-unsaturated acyl chlorides

“…From this study, it was found that the cross-coupling reaction produced moderate conversion in N,Ndimethylacetamide (DMA), 1,2-dimethoxyethane (DME), N,Ndimethylformamide (DMF) and tetrahydrofuran (THF) solvents (entries 1-4). Under similar conditions, the conversion was good in acetonitrile and 1,4-dioxane solvents furnishing 69-71% of isolated yields of chalcone (entries [5][6]. Additional screening in the presence of inorganic bases produced 69-79% (entries 7-10), while pyridine as a base produced 66% conversion under similar conditions (entry 11).…”

“…The coupling constants (J) are reported in Hertz (Hz). a,b-Unsaturated acyl chlorides were prepared using the reported procedures [6]. Triarylbismuths were prepared using standard protocols [7].…”

“…Compounds containing chalcone functionality are well known for their important medicinal properties in addition to their utility for a variety of transformations in organic synthesis [4]. In principle, the direct cross-coupling of a,b-unsaturated acyl chlorides with organometallic reagent under metal catalysis is an ideal and a facile pathway to access chalcones, since a,b-unsaturated acyl chlorides are easily obtainable substrates [5,6]. Indeed, the traditional method of preparation of chalcones via Claisen-Schmidt reaction or Friedel-Crafts acylation protocols often produce unwanted side reactions in the presence of additional acid or base sensitive groups [4].…”

Model Studies Towards Stephaoxocanes: Construction of the 2‐Oxa‐4‐aza‐ phenalene Core of Stephaoxocanidine and Eletefine

“…In the hope that amination of benzylic halide 17 would lead to successful CϪN bond formation, alcohol 14 was halogenated with the novel thionyl chlorideϪbenzotriazole reagent; [29] however, only low yields of 17 (15Ϫ20 %) were obtained. The non-inverted sulfite was the major reaction product, presumably because of steric crowding at the benzylic position.…”

Synthesis, structure, and antimycobacterial activity of 6-[1(3H)-isobenzofuranylidenemethyl]purines and analogs

“…2 The following compounds were prepared according to literature procedures: 2-chloro-6-(2-furyl)-9-(4-methoxyphenylmethyl)-9H-purine 1d, 2d (Z)-9-benzyl-6-[isobenzofuran-1(3H)-ylidenemethyl]-9H-purine 3a, 2 2,6-dichloro-9-(4-methoxyphenylmethyl)-9H-purine 8, 2d (E)-tributyl(phenylethenyl)stannane, 9 tributyl(benzo[b]fur-2-yl)stannane, 10 and furfuryl chloride. 11 Benzylzinc chloride was generated from benzyl chloride and Rieke zinc 12 according to a published procedure 6 and the concentration of the solution was determined by hydrolysis and iodolysis. 13 Furfurylzinc chloride was generated from furfuryl chloride following the same protocol.…”